Ethyl formate → rac. 4-Benzyloxy-3-methylbutanal

HRID 1277532Notes

Reaction equation

HRID 1277532 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([CH3:14])[CH2:11][C:12]#N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.C(OCC)=[O:26].[Cl-].[NH4+]>C1(C)C=CC=CC=1.CCCCCC>[CH2:1]([O:8][CH2:9][CH:10]([CH3:14])[CH2:11][CH:12]=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8025Ethyl formateHCID 25517Ammonium ChlorideHCID 109762734-(Benzyloxy)-3-methylbutanenitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 14658350rac. 4-Benzyloxy-3-methylbutanal

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

A solution of 5.8 g. (0.0307 mole) of rac. 4-benzyloxy-3-methylbutyronitrile in 290 ml. of hexane was stirred at -65° C. to -70° C. while 22.4 ml. (4.78 g.; 0.0337 mole) of 25% diisobutylaluminum hydride solution in toluene was added dropwise. Theresulting solution was stirred at -65° C. to -70° C. for 0.5 hours then at room temperature for 5 hours whereupon 2.8 ml. of ethyl formate was added dropwise. The reaction mixture was then treated with 250ml. of saturated aqueous ammonium chloride solution. Stirring was continuedfor 20 minutes at which point 125 ml. of 5% by weight aqueous sulfuric acidwas added and stirring was continued for an additional 10 minutes. The organic layer was separated and the aqueous layer was extracted with ether. The organic solutions were combined and processed as in Example 1 giving 4.79 g. (81.3%) of rac. 4-benzyloxy-3-methylbutanal as a yellow oil.

Workup

  1. waitat room temperature for 5 hours whereupon 2.8 ml
  2. additionThe reaction mixture was then treated with 250ml
  3. stirringStirring
  4. waitwas continuedfor 20 minutes at which
  5. additionof 5% by weight aqueous sulfuric acidwas added
  6. stirringstirring
  7. waitwas continued for an additional 10 minutes
  8. customThe organic layer was separated
  9. extractionthe aqueous layer was extracted with ether

Sources & evidence

ORD record
ord-ee60592bf1db48539030db9de33a8681
Source dataset
uspto-grants-1981_07
Patent number
US04277610

Reaction notes

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